Figuring out directions (driving, walking, transit) is actually quite easy in most cities. My approach is to just lump specific places into general "areas", get familiar with how to get between areas (transit/driving options) by thinking about their absolute positions and connections that exist, and then for unfamiliar places, look it up on a map before leaving.
The only thing I miss with navigation is real-time traffic. Which, all things considered, is just a "nice to have".